The stretch of Highway U.S. 1 that connects the Florida mainland to Key West is known for blue ocean views that reach to the horizon, world class fishing, fiery red sunsets, and water adventures both on top of and below the water. But this road trip is also wrapped in funky fun. Where else can you ride through the water on a famous movie set, have a tarpon jerk the bait from your hands as you kneel on a dock or watch fire eaters at sunset? And did I mention that key lime pie is available for breakfast, lunch and dinner? Let's hit the road for some funky Florida fun on the way to Key West. And, yes, we'll be tasting key lime pie at every opportunity.
Miami makes a good start for your Florida Keys road trip. Fly into Miami International Airport, rent a convertible and hit the road!
Mile Marker 100, Key Largo, FL, US
Would you like to cruise on a movie set? At Longboat Key, hop aboard the original vessel used in the filming of "The African Queen." When Captain Lance Holmquist stokes the steam engine, you'll chug a chug chug along a Key Largo canal on the 1.5-hour journey to the Atlantic Ocean and back. Or book a 2-hour dinner cruise that stops at Pilot House Restaurant for a 3-course meal. Yes, they serve Key Lime Pie for dinner.
81600 Overseas Hwy, Islamorada, Village of Islands, FL, US
At Morada Bay Beach Cafe in Islamorada, outdoor dining comes with a blazing sunset. Sit at a colorful table on a sandy beach as slow jazz serenades from a loudspeaker. I recommend the coconut-crusted mahi mahi accompanied by coconut rice and broccolini, an excellent blend of Caribbean and American tastes. You'll want to order key lime pie for dessert, of course. If the scene looks eerily familiar, you're dining on one of the film sets of the Netflix drama series, "Bloodline."
82100 Overseas Highway, Islamorada, Village of Islands, FL, US
Islamorada deserves a couple of days for exploration (or more, if you have the time). Islander Resort, A Guy Harvey Outpost makes a fun headquarters. Accommodations include full kitchen, screened lanai, picnic tables and outdoor grills. You'll want to save time in your busy schedule for an afternoon or morning for lounging on the resort's sandy beach.
77520 Overseas Hwy, Islamorada, Village of Islands, FL, US
Want to feed a hungry tarpon? You can do it at Robbies Marina. Purchase a bucket of bait, then kneel on the dock as tarpon compete to yank the bait from your hand. Of course you'll also want to browse the eclectic mix of outdoor shops. When you're done shopping, stop in at the aptly names The Hungry Tarpon for a margarita, fish tacos and, you guessed it, key lime pie.
83413 Overseas Hwy, Islamorada, Village of Islands, FL, US
You can't come to the Florida Keys without offshore fishing. Head on over to Whale Harbor Charter & Marina in Islamorada. Spend the afternoon with Capt. Skip Bradeen on the Blue Chip Too where the fishing comes with stories of Capt Skip's 50 years of fishing in the Florida Keys.
79867 Overseas Hwy, Islamorada, Village of Islands, FL, US
Did you catch any fish with Capt. Skip? Head on over to Lazy Days Restaurant where the chef will cook up your catch. Did your line come up empty? That's okay, you can order from the menu. And there's key lime pie for dessert, too.
Marathon, FL, US
After a couple of days hanging out in Islamorada, it's time to continue this Florida Keys road trip. In Marathon, stop to walk the Seven Mile Bridge, listed on the National Register of Historic Places. Originally a railroad line constructed by Henry Flagler, the right of way eventually became a bridge on the Overseas Highway. At one time, Seven Mile Bridge was the longest bridge in the world. No longer drivable, cyclists and pedestrians are the only traffic. It's a great spot for photography, too.
1791 Bogie Drive, Big Pine Key, FL, US
There's still time for a water adventure before arriving in Key West. Why not stop at Big Pine Key for a kayaking adventure? You don't have to be an expert to explore here. Meet Bill Keogh of Big Pine Kayak Adventures at Old Wooden Bridge Fishing Camp for a 3-hour paddle through the mangroves at No Name Key. After the the adventure's over, look for the endangered key deer that live on Big Pine Key.
6810 Front St, Stock Island, FL, US
After walking the Seven Mile Bridge and kayaking at Big Pine Key, you're bound to be hungry. That's why you're stopping at Hogfish Bar & Grill on Stock Island for lunch. Order up a hogfish sandwich (a delicate fish caught by divers). Finish off lunch with a slice of key lime pie.
3824 N Roosevelt Blvd, Key West, FL, US
If you appreciate hip, sophisticated lodging that's a bit removed from the noise and hustle-bustle, The Gates Hotel Key West will hit your sweet spot. From the welcome rum drink to the sleek furnishings to an awesome pool, The Gates Hotel makes a fun choice. And it's on one of the trolley stops so you can leave the car in the parking lot when exploring the historic sights of Key West.
1 Whitehead St, Key West, FL, US
Set your watch to arrive at Key West's Mallory Square about two hours before sunset. You'll be treated to a quirky experience complete with street performers, arts and crafts booths, food trucks, and plenty of other tourists. A hush comes over the crowd when the blazing sunset makes an appearance. Bet you can't resist from oohing and ahhing as the fiery red ball dips behind Sunset Key.
410 Wall St, Key West, FL, US
After the Mallory Square fun, a short walk takes you to an authentic Cuban dinner at El Meson de Pepe. I recommend the Ropa Vieja, “traditional Cuban shredded beef stewed with fresh tomatoes, green peppers, onions and red wine.” And no day in Key West should ever end without a slice of Key Lime Pie.
729 Thomas St, Key West, FL, US
After a restful night at the Gates Hotel, let's go for a breakfast that will take you to heaven on Thomas Street, Blue Heaven, that is. You'll probably encounter a line, but the Lobster Benedict is worth it. And so is the Key Lime pie.
122 Simonton St, Key West, FL, US
907 Whitehead St., Key West, FL, US
1316 Duval St, Key West, FL, US